Nitration of sugars



Patented Apr. 28, 1936 UNITED STATES NITRATION F SUGABS Joseph A.

Wyler, Allentown, Pa., assignor to Trojan Powder Company, a corporation of New York No Drawing. Application May 25, 1934, Serial No. 727,591

3 Claims. (01. 52-20) My invention relates to improvements in the nitration of sugars, and more particularly relates to improved means for the purification of the products obtained by the nitration of sugars by 5 the action of nitric acid or nitrating acids. One of the objects of my invention is to provide means for the purification and stabilization of the gummy and doughy acid products which are obtained as the result of the nitration step.

Tne nitration of cane sugar and similar sugars dissolved in glycerin, glycol, and other polyhydric alcohols is well known. In the manufacture of these products the usual procedure is to dissolve the sugar in the alcohol and to then nitrate the mixture, and up to the present time the difficulties inherent in the nitration of the sugars alone has prevented their commercial preparation, as the physical conditions of the nitrated products have been such as to prevent their purification to a sufficient extent to enable a stable product to be obtained by the methods of purification and stabilization heretofore used.

I have discovered that by nitrating a sugar in the usual manner employed in the nitration of other materials, (and without the presence of any solvent fornitrated sugar except the nitrating acids themselves) and thereafter separating the resulting gummy, viscous nitrated sugar layer and admixing it with a suitable solvent for nitrated sugar which is insoluble in water or in the dilute spent acid, it is possible to obtain a solution of the nitrated sugar in condition suitable for further purification.

In the practice of my invention I may employ such solvents as mononitrobenzene, mononitrotoluene, mononitroxylene, alkyl nitrates, aliphatic ethers, chlorinated aliphatic ethers, chlorinated paraffins, alkvl carbonates, nitrated esters of hy- 0 droxy acids such as nitrated methyl glycolate, nitrated methyl lactate, nitrated methylmalate, nitrated dimethyltartrate, etc. and in general I may employ in the practice of my invention any material which is combustible and oxygen-deficient and which is insoluble in water and unaffected by dilute spent acid, and which is a solvent for nitrated sugar. In the above list where I have mentioned the methyl compounds for example, I may also employ the ethyl compounds or the other homologues of the compounds named.

I As an example of my invention, I will describe the process which I prefer to employ in the treatment of a sugar such as cane sugar, glucose, lactose, levulose, and the like. a

55 To parts, by weight, of 98% HZNOa, add. 30

parts, by weight, of sugar, keeping the temperature below 20 C. When all of the sugar has been dissolved, add 300 parts of oleum or strong H2504. This forms either a thick, gummy plastic mass or a. viscous solution in suspension in the spent acid. 5 This suspension is drowned in tap water and stirred a few minutes in order to free alarge portion of its occluded acid. Then add 15 parts of mononitrobenzene and stir. This results in a thin solution of nitrated sugar in the agent added, 10 which can be washed, stabilized and settled, by the methods commonly used in the washing and stabilizing of nitroglycerine and other liquid organic nitrates.

It will of course be recognized that the above 15 is given as an illustration only, and my invention is not to be limited to the specific proportions named. In general, my invention may be applied to the treatment of cane sugar, glucose, levulose, maltose, lactose, etc. as well as any of the glyco- 20 ides derived from these sugars.

The products obtained from the practice of my invention are liquids which are capable of use in the formulation of explosive mixtures as substitutes for the nitrated polyhydric alcohols and in 25 general the products obtained by the practice of my invention may be employed to advantage either directly as liquid explosive materials or indirectly in the preparation of explosive mixtures, in combination with the usual constituents of for- 30 mulated explosives.

It will be evident that many modifications may be made within the. limits of the disclosure as herein made, and accordingly no limitations should be placed upon my invention, except as 35 indicated in the appended claims.

I claim:

1. The process of treating an organic body selected from the group of a sugar and the glycoside 40 of a sugar, which comprises nitrating the material, separating the plastic viscous nitrated material from the spent acid, adding a water-insoluble combustible and oxygen-deficient organic solvent for the nitrated material which solvent is unai- 4,5 iected by dilute spent acid, and thereafter washing and stabilizing the mixture so obtained.

.2. The process of treating an organic body selected from the group of a sugar and the glycoside of a sugar which comprises nitrating the material, 5 separating .the plastic viscous nitrated material from the spent acid, adding a water-insoluble solvent selected from the group of mononitrobenzene, mononitrotoluene, mononitroxylene, alkyl nitrates, aliphatic ethers, chlorinated aliphatic 5 of a sugar which comprises nitrating the material, separating the plastic viscous nitrated material from the spent acid, adding a solvent nitrated ester of an aliphatic hydroxy acid, and

thereafter washing and stabilizing the mixture so 5 obtained.

JOSEPH A. WYLER. 

